Sodium Hydroxide → 4-((1-(Tert-butoxycarbonyl)piperidin-4-YL)oxy)-2-methoxybenzoic acid

HRID 1292035ノート

反応式

HRID 1292035 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 10570851Tert-butyl 4-(3-methoxy-4-(methoxycarbonyl)phenoxy)piperidine-1-carboxylate

生成物 1

HCID 105458744-((1-(Tert-butoxycarbonyl)piperidin-4-YL)oxy)-2-methoxybenzoic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
70 °C

実験手順

Methyl 4-(N-t-butoxycarbonyl-4-piperidinyloxy)-2-methoxybenzoate (35 g, 96 mmol) from Step 5 above was dissolved in MeOH (250 mL) and to the solution was added 2 N NaOH (100 ML, 200 mmol). The stirred mixture was warmed to 70° C. for 3 h. The solution was cooled to ambient temperature, concentrated under reduced pressure, cooled to 0° C. and 0.5M aqueous citric acid solution (300 mL) was added. To the suspension was added EtOAc (500 mL) and water (300 mL). The EtOAc layer was separated and the aqueous phase was washed with EtOAc (200 mL). The combined EtOAc layers were washed with brine (250 mL), dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 4-(N-t-butoxycarbonyl-4-piperidinyloxy)-2-methoxybenzoic acid as a foam that solidified on standing in vacuo (HPLC (method A) retention time= 8.46 min).

後処理

  1. temperatureThe solution was cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. temperaturecooled to 0° C.
  4. addition0.5M aqueous citric acid solution (300 mL) was added
  5. additionTo the suspension was added EtOAc (500 mL) and water (300 mL)
  6. customThe EtOAc layer was separated
  7. washthe aqueous phase was washed with EtOAc (200 mL)
  8. washThe combined EtOAc layers were washed with brine (250 mL)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-63a764325c2d43669d97a80387ab8545
出典データセット
uspto-grants-1998_05
特許番号
US05756497

反応ノート

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